Synthesis of methyl 3-O-(alpha-D-glucopyranosyl)-7-O-(L-glycero-alpha-D- manno-heptopyranosyl)-L-glycero-alpha-D-manno-heptopyranoside.
The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.
Garegg
P J
PJ
Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.
Oscarson
S
S
Szönyi
M
M
D002240:Carbohydrate Sequence; D008070:Lipopolysaccharides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012475:Salmonella / Q000032:analysis; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D008070:Lipopolysaccharides; D008759:Methylglycosides; D014312:Trisaccharides; C067060:methyl 3-O-glucopyranosyl-7-O-heptopyranosyl-heptopyranoside